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A guide to sailing the Caribbean: Cruise away to paradise


9 August, 2023


6 March, 2024

A guide to sailing the Caribbean: Cruise away to paradise

Perfect winds, calm waters, islands that are the very epitome of a tropical paradise – there’s nothing quite like sailing in the Caribbean. This magical cluster of islands is not only renowned for boasting some of the world's most beautiful villas, but is also where sailors of all abilities come to make the most of the incredible conditions. The trade winds blow all year round, ensuring you're never becalmed, and the countless little coves and inlets are yours to discover at your leisure.

If you've always wanted to sail around the Caribbean, this guide will help you take the plunge, hoist your own sail, and make that dream a reality. We’ll look at practical aspects of cruising the Caribbean, such as the best time of year to sail and what to watch out for if you're new to these waters.

Our Caribbean sailing guide is your introduction to the wonders of this stunning region. If it's your first time sailing, we promise it won't be your last as you discover the natural beauty, the warmth and friendliness of the welcome, and the sheer exhilaration of letting the wind take you on a journey as you sail the Caribbean islands.

Sailing conditions: Best time and place

The Caribbean is a large and diverse region with a wide range of weather patterns and seasons. Don't be fooled into thinking that the weather around Barbados will be the same as you experience in Anguilla or St Martin, for example.

To get the best out of sailing in the Caribbean, you need to factor in the climate of the area you're sailing in, the wind speed and direction, if the area is vulnerable to storms and hurricanes, and the time of year. Let’s take a look at the considerations you need to include in your plans and the best time to sail the Caribbean:

The climate and temperature

Overall, the best time to sail in the Caribbean is between December and April. This is when the weather is dry and sunny, and you have the least likelihood of storms or hurricanes. You may encounter the occasional squall, but even this is rare.

The Caribbean's trade winds are consistent all year round, blowing from east to west. There are occasional days when the winds drop to a mere breeze, but even this should be enough to get you from island to island if you don't have the advantage of an outboard motor.

The climate of the Caribbean is tropical, but because of the topography of the ocean and the islands, you can experience ‘micro-climates’ where some locations will be hotter than others. At sea level, the average temperature ranges between 24-32°C (75-89°F).

The wind speed and direction of each area

The trade winds blow from east to west throughout the Caribbean. They fluctuate in strength, with the strongest winds blowing around December and January. These are known as the Christmas winds and are ideal if you're a more experienced or intermediate sailor.

During June to November, when the Caribbean is going through its 'wet' season, the trade winds tend to be weaker and less stable, making sailing conditions unpredictable.

Other winds that affect sailing in the Caribbean include the easterly alisio and the northeasterly alize. If you find yourself heading towards Cuba, watch out for the powerful bayamo wind that blows along the island's southern coast.

The hurricane season and its impact on each area

1st June marks the start of the hurricane season in the Caribbean, which runs to the end of November. Hurricanes are violent storms that can have exceptionally strong and dangerous winds, cause significant storm surges, and damage property. Hurricanes are classified into categories, the higher the number, the more damaging and dangerous the storm.

Hurricanes rarely make landfall, but when they do the impact can be severe. If you’re sailing in the Caribbean during this period then it’s vital to stay updated with the latest hurricane forecast.

Our advice is to avoid sailing the Caribbean during the hurricane season. Even the most experienced of sailors will head to port at the first mention of an impending hurricane

The peak season and its impact on prices, crowds, and availability

It's not just about the weather – the holiday season in the Caribbean will have a big impact on the price of yacht hire and availability, too.

During the Caribbean Regatta season, you may find that hiring a yacht is more challenging as everyone wants to join in with the festivities. There are a finite number of yachts for charter in the Caribbean. While the larger islands, such as Barbados, will have greater availability, the demand during the peak holiday season will be considerably higher.

Where to sail in the Caribbean

Where you sail in the Caribbean will also depend on a few specifics including:

· Your sailing skill level and experience

· Your preferred sailing style and duration

· Your interests and goals

If you’re a new sailor with very limited experience, the options are to either ensure your charter yacht comes with an experienced skipper who can navigate the waters for you, or choose relatively trouble-free areas with calm waters. Here are our top three locations for sailing in the Caribbean:


The gentle trade winds that surround Jamaica provide ideal conditions for a leisurely sail around the coast of this vibrant Caribbean island. Navigate the crystal-clear waters and discover the hidden coves and secluded bays dotted around the 1022km of coastline, and drop anchor to get up close to the coral reefs that are beautiful moving pictures of marine life.

On the north side of the island, Doctor’s Cave Beach will welcome you for a stop-off to enjoy its white sands and turquoise waters, and just down the coast from here is Montego Bay Marine Park Trust for wonderful bird-watching and glass bottom boat tours.

British Virgin Islands

The BVIs are truly heavenly. This cluster of islands lies in a calm, tranquil spot where even novice sailors can explore the coastline at their leisure. Tortola is the largest of the BVIs.

You'll need to sail around to the north coast of the island to find the best beaches, including Smuggler's Cove (doesn't every island have at least one Smuggler's Cove?), Lambert Beach and Brewer's Bay. The southern side of the island has calmer waters and is ideal for new sailors, although it can get busy during the regatta season.

Turks & Caicos

With untold opportunities to discover your own little slice of tropical heaven, the Turks & Caicos islands are ideal for sailing in the Caribbean. Crystal-clear waters and gentle winds take you on a journey around the islands, from Providenciales to North Caicos.

On the way, you can stop and visit the iguana sanctuary at Little Water Cay, or spot the cannons of long-lost ships in Fort George Bay. Conditions are calm and the channels between the islands are easy to navigate.

Planning your sailing itinerary

Before you book a villa in the Caribbean and charter a yacht, you may need to do a little more planning than usual. If you’re a complete novice, it may be worth taking a sailing course before you set off so you can get to grips with the basics of sailing a yacht with both sails and an outboard motor.

It’s also wise to familiarise yourself with how to read a chart and understand ‘sailing etiquette’, especially in the harbour. This isn't just about good manners and showing respect for your fellow sailors. It's also about safety protocols and ensuring nobody is put in danger when manoeuvring a yacht into a mooring, for example.

Remember to check the weather forecast before you set off and ideally to plan your Caribbean sailing trip during the dry season.

Choose your vessel according to your capabilities. Larger vessels can be more challenging to sail if you're a novice. If you're more experienced, a larger schooner may be suitable so that you get the best experience.

Head off the beaten track

While seasoned sailors will pick some of the more well-known destinations to drop anchor, such as St Barts, Grand Cayman, Jamaica and the U.S Virgin Islands, plenty of lesser-known anchorages offer a unique experience.

St John is one of the quieter Caribbean islands and better suited to those who want to explore and be at one with nature. Cruz Bay is a popular stop-off point for refreshments and provisions, and many use this as an opportunity to take a ferry to neighbouring St Thomas to explore its Coral World Ocean Park. Alternatively, head inland and hike from one of St John’s many beaches to the mountain top, or pop your snorkel gear on and explore the underwater trail at Trunk Bay.

Look for destinations that offer secluded beaches, pristine dive sites, and off-the-beaten-path attractions. That’s the beauty of sailing around the Caribbeanyou can find your own little piece of paradise far from the usual tourist spots.

Sailing tips and tricks

· Always check the weather forecast before you set off. Squalls and small storms can blow up even during the dry season. If the weather looks inclement, stay on shore and go exploring or check out the restaurants and shopping instead.

· Go island hopping around the smaller islands. Be sure that you understand how to read a chart so you can navigate the channels safely and stay away from shallows or reefs.

· Even in the best conditions, sailing can be challenging, especially if you have members of your party who are not strong swimmers. It’s essential that enough life jackets are on board and that everyone knows where they are in case of an emergency.

· Prepare your yacht before you go out. If you have an outboard motor, ask a marine engineer to check it over to see that it’s running correctly. Check the jerry cans are full and that you’ve got enough fuel for your journey.

· Explore the French Caribbean islands of St Barts, Martinique and Guadeloupe for a change of pace and a mix of Creole and French culture that's unique to this part of the world.

· Always let someone onshore know your itinerary, where you intend to sail, and your arrival time and date.

Plan your Caribbean getaway with onefinestay

With endless family-friendly villas in the Caribbean waiting to be discovered, onefinestay is your gateway to one of the most vibrant destinations in the world. Browse our travel guides to find out more or speak to our Travel Advisors who will match you with the dream Caribbean villa for your sailing trip.